3,4,5-Trimethoxybenzoic Acid → N-Boc-pyrrolidine

HRID 1992740Notes

Reaction equation

HRID 1992740 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1CCNCC(C)=CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCC[C@H]1C(O)=O.COC1C=C(C=C(OC)C=1OC)C(O)=O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 145742L-ProlineHCID 72524883HCID 72524883, compound

Product 1

HCID 643455N-Boc-pyrrolidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the compound 2-[2-(2-Methyl-3-phenyl-allylamino)-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared from racemic proline according to the scheme1), 0.6 g (2 mmol) and 3,4,5-trimethoxy benzoic acid 0.513 g (2.4 mmol) in dry dichloromethane 10 ml, triethyl amine 0.2 ml was added and stirred at room temperature for 20 min. Then was added O-(benzotriazole-1-yl)-N,N,N′,N′-tetramethyl uranium tetrafluoroborate 1.3 g (4 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM and was washed with 10% NaHCO3 solution, water and brine, dried, concentrated and subjected to column chromatography silica gel using CHCl3/MeOH as eluent to obtain 1 g of 2-{2-[(2-Methyl-3-phenyl-allyl)-3,4,5-trimethoxy-benzoyl)-amino]-ethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. washwas washed with 10% NaHCO3 solution, water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f1cedf7bab8446258c1341ea68bbbb8a
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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